1-Nitro-1-(phenylthio)propene as a New Nitro Olefin Reagent for 3-Methylfuran Annulation and Its Application to the Synthesis of Some Furanoterpenoids

Journal of Organic Chemistry

Volumn 45, Issue 15, 1980, Pages 2945-2950

  Miyashita, Masaaki ^a   Kumazawa, Toshiaki ^a   Yoshikoshi, HIROSHI Akira ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001553831     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo01303a005     Document Type: Article

References (28)

1. For general reviews on the syntheses and chemistry of aliphatic nitro olefins, see: (a) Baer, H. H.; Urbas, L. “The Chemistry of the Nitro and Nitroso Groups”; part 2, Feuer, H., Ed.; Interscience: New York, 1970; Part 2, pp 75-200
2. Müller, E., Ed.; “Methoden der Organischen Chemie (Houben-Weyl)”; Georg Thieme Verlag: Stuttgart, 1971; Vol. 10/1, pp 9-462
3. Kochany, J. Wiad. Chem. 1978,32,723
4. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1.
5. Review: Larson, H. O. “The Chemistry of the Nitro and Nitroso Groups”; Feuer, H., Ed.; Interscience: New York, 1969; Part 1, pp 316-324
6. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
7. Yanami, T.; Kato, M.; Yoshikoshi, A. J. Chem. Soc., Chem. Commun. 1975, 726
8. Miyashita, M.; Yanami, T.; Yoshikoshi, A. J. Am. Chem. Soc. 1976, 98, 4679
9. Yanami, T.; Ballatore, A.; Miyashita, M.; Kato, M.; Yoshikoshi, A. J. Chem. Soc., Perkin Trans. 1 1978, 1144
10. Yanami, T.; Ballatore, A.; Miyashita, M.; Yoshikoshi, A. Synthesis, in press.
11. Patterson, J. W.; McMurry, J. E. J. Chem. Soc. D 1971, 488. Ranganathan, S.; Ranganathan, D.; Mehrotra, A. K. J. Am. Chem. Soc. 1974, 96, 5261. Ehrig, V.; Seebach, D. Chem. Ber. 1975, 108, 1961. Seebach, D.; Leitz, H. F.; Ehrig, V. Synthesis. 1975, 108, 1924. Seebach, D.; Ehrig, V.; Leitz, H. F.; Henning, R. Synthesis. 1975, 108, 1946. Pitacco, G.; Risaliti, A.; Trevisan, M. L.; Valentin, E. Tetrahedron 1977, 33, 3145. Grieco, P. A.; Ohfune, Y. J. Org. Chem. 1978, 43, 2720. Danishefsky, S.; Prisbylla, M. P.; Hiner, S. J. Am. Chem. Soc. 1978, 100, 2918.
12. Preliminary communication: Miyashita, M.; Kumazawa, T.; Yoshikoshi, A. J. Chem. Soc., Chem. Commun. 1978, 362.
13. Preliminary communication: Miyashita, M.; Kumazawa, T.; Yoshikoshi, A. Chem. Lett. 1979, 163.
14. Henry, L. Bull. Soc. Chim. Fr. 1895, 13, 999. An improved procedure was used in this work (see Experimental Section).
15. Pfeffer, P. E.; Silbert, L. S. Tetrahedron Lett. 1970, 699. BuLi was used here to generate the dianion in place of lithium diisopropylamide as proposed by the original authors.
16. During the course of this study, an alternative preparation of 7 was reported, although detailed results were not given: Seebach, D.; Lehr, F. Angew. Chem. 1976, 88, 540.
17. Melton, J.; McMurry, J. E. J. Org. Chem. 1975, 40, 2138.
18. Baskov, Y. V.; Urbañsky, T.; Witanowski, M.; Stefanik, L. Tetrahedron 1964, 20, 1510.
19. Batty, J. W.; Howes, P. D.; Stirling, C. J. J. Chem. Soc. D 1971, 534; J. Chem. Soc., Perkin Trans. 1 1973, 65. Howes, P. D.; Stirling, J. M. Org. Synth. 1973, 53, 1.
20. Birch, A. J.; Richards, R. W. Aust. J. Chem. 1956, 9, 241 and references cited therein.
21. For alternative syntheses of evodone, see: (a) Stetter, H.; Lauterbach, R. Angew. Chem. 1959, 71, 673
22. Stetter, H.; Lauterbach, R. Chem. Ber. 1960, 93, 603
23. Moiseekov, A. M.; Lakhvich, F. A.; Akhrem, A. A. Aktual. Probl. Izuch. Efirnomaslichn. Rost. Efirnykh Masel Tezisy Dokl. Simp., 2nd 1970, 159; Chem. Abstr. 1972, 76, 99847.
24. Ishii, H.; Tozyo, T.; Minato, H. Tetrahedron 1965, 21, 2605. Tada, M.; Moriyama, Y.; Tanahashi, Y.; Takahashi, T. Bull. Chem. Soc. Jpn. 1974, 47, 1999.
25. Tada, T.; Takahashi, T. Tetrahedron Lett. 1973, 3999.
26. Danishefsky, S.; Kitahara, T. J. Org. Chem. 1975, 40, 538.
27. For analogous examples, see: Nozoe, T.; Cheng, T. S.; Toda, T. Tetrahedron Lett. 1966, 3663. Miyashita, M.; Uda, H.; Yoshikoshi, A. Chem. Commun. 1969, 1396.
28. Marshall, J. A.; Andersen, N. H. J. Org. Chem. 1966, 31, 667. Marshall, J. A.; Cohen, C. M. Tetrahedron Lett. 1966. 1971, 36, 877.